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One of my favorites is spending nearly 10 minutes trying to get someone to read a single word on their screen correctly, in a dialog box that was blocking them, containing fewer than 10 words, so I could find the cause of their problem. After nearly 30 minutes to figure out that they had a popup blocking them, and not "the computer doesn't work".

What eventually worked was getting them to spell it to me backwards. That strategy has worked out quite well in other cases too - I suspect because it avoids some of people's built-in autocorrect and dyslexia (autoincorrect).

(I honestly mostly enjoy tech support, and I've done it for many years, sometimes professionally. But some people do seem like lost causes, and are not just having a bad day)

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The flip side of this is the pleasant surprise of working with a near-retirement age grandma who assures you that she "isn't technical" and "doesn't know how to use a computer", but will studiously write down every keyboard shortcut on little post-it notes and add it to their collection like they're porcelain cats she found at the Sunday markets. I've watched some of these people operate a computer in a manner reminiscent of watching an F1 driver at work, the screen just a blur as their fingers dance over the keyboard.
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Absolutely, the ones that are clearly trying more than make up for the rest imo, and some are stunning. There are a lot of them. And many of the rest are just having a bad brain day and need help rubber-ducking to see the thing right in front of them - we've all been there, many times.
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There's a selection effect here in that smart-enough users won't bother contacting support if they work around an issue on their own, or if something is actually a non-issue for 99%+ of the user base. The ratio of usage and support contacts can be monitored. I fear a lot of devs develop unproductive mental models of the user purely from a minority sample.
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